2'-Aminoacetophenone → 2-Amino-alpha-methylbenzenemethanol

HRID 1534485Notes

Reaction equation

HRID 1534485 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11]>CO>[OH:12][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3])[CH3:11]

Participants

4

Reactant 2

HCID 110862'-AminoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 1120582-Amino-alpha-methylbenzenemethanolYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (40 g, 1.0 mol) was added portion wise to a stirred solution of o-aminoacetophenone (80 g) in methanol (800 ml) at 0°, allowing the effervescence to subside between each addition. Cooling was removed and the mixture allowed to warm to reflux temperature to complete the reaction. When cool, the solvent was evaporated and the residue partioned between dichloromethane-water. The organic solution was washed successively with water and brine, dried (anhyd. MgSO4), filtered and evaporated to a light yellow oil which crystallized from petroleum spirit (40°-60°) to give white crystals (52 g, 64%), m.p. 50°-52°.

Workup

  1. additionto subside between each addition
  2. temperatureCooling
  3. customwas removed
  4. temperatureto warm
  5. temperatureto reflux temperature
  6. customthe reaction
  7. temperatureWhen cool
  8. customthe solvent was evaporated
  9. washThe organic solution was washed successively with water and brine
  10. dry with materialdried (anhyd. MgSO4)
  11. filtrationfiltered
  12. customevaporated to a light yellow oil which
  13. customcrystallized from petroleum spirit (40°-60°)

Sources & evidence

ORD record
ord-e09b0e34a6584703987db3800aaaedf7
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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